Benzylamine → 6-Aminoundecane

HRID 1031408Notes

Reaction equation

HRID 1031408 reaction equation
[CH2:1]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=O)[CH2:2][CH2:3][CH2:4][CH3:5].C([NH2:20])C1C=CC=CC=1>[Pd]>[CH3:5][CH2:4][CH2:3][CH2:2][CH2:1][CH:6]([NH2:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 135616-Undecanone

Product 1

HCID 1418456-AminoundecaneYield 75.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Diamylketone (12 g) was hydrogenated at 50 psi in the presence of 10% Pd/C (1.5 g) and benzylamine (8.31 g) at room temperature for 6 hours. Further catalyst (1.5 g) was added and the mixture was hydrogenated at 40° for 5 hours. The reaction mixture was filtered and evaporated to dryness (combined with the product from a previous 12 g hydrogenation). The oil was purified by column chromatography to give 6-undecylamine as an oil (9.1 g, 38%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness (
  3. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-dc6fae985ef3493ebaec31f61c057f86
Source dataset
uspto-grants-1990_09
Patent number
US04954339

Reaction notes

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